[3] Produced by Jon Brion, it was expected to be released in 2003 but was delayed several times by the record label without explanation, leading to speculation that a dispute had arisen over its commercial appeal.

In collaboration with producers Mike Elizondo and Brian Kehew, Apple re-recorded the album over 2004 and 2005, and it was eventually released more than three years after the original recording sessions began.

With the album half complete in April 2003, Brion, Apple and Biller worked at Cello Studios, and a new release date of July 22 was announced.

Brion and Apple then travelled to England later that month, to record strings and orchestration for the songs at Abbey Road Studios in London.

The slow-paced track "Extraordinary" was referred to as "a Tin Pan Alley-esque blend of Tom Waits and Vaudeville", while the much more energetic "Better" was described as "an OutKast-like deluge of beats".

Josh Korr of the Tampa Bay Times wrote, "With a playfulness and penchant for odd sounds and instruments that channel the spirit of Brian Wilson's Smile, Apple's first songs since 1999 make Norah Jones, Joss Stone, Alicia Keys and other pretenders sound like American Idol rejects",[10] while Entertainment Weekly called the songs "tantalizing, brazenly eccentric art pop ... With Apple, the weirder, the better".

They received a positive review from The New York Times, who described the album as "an oddball gem", adding "Had it been released, Extraordinary Machine would have been a fine counterbalance to a pop moment full of monolithic, self-righteous sincerity.

"[18] Ed Bumgardner concurred, saying the album was "certainly a work of daring and sophistication, as wildly imaginative as it is entertaining",[19] while Will Dukes said "Extraordinary Machine flaunts a quirky, cold-world cohesiveness that's as inviting as it is alienating.

Entertainment Weekly reported in its June 24, 2005 issue that Apple was preparing work on a "second third" album with producer Brian Kehew of the electronica band The Moog Cookbook,[24] further fueling speculation amongst fans that the leaked Machine tracks had been shelved indefinitely.

A July 2005 online chat, little noticed at the time, occurred with hip hop musician Questlove on a website devoted to The Roots.

Elizondo had played bass on two When the Pawn tracks, but one reporter had described him as "a curious departure from Brion" because of his more well-known production work with popular hip hop artists such as 50 Cent, Dr. Dre and Eminem.

[6] Speaking with Billboard, Elizondo acknowledged that it was "a little disheartening" to be working with the knowledge that Brion's version was available to the public, but applauded Apple's "amazing core of fans" for their efforts to have the album released: "The way they interpreted it was, the label isn't putting out her record, so we're going to do it for her.

Despite rumors that the album had caused a rift between Brion and Apple, they performed together at Largo the Friday evening before Epic's announcement.

I remain a fan and think she's great, and she shouldn't have to meet too much resistance"; meanwhile, Elizondo insisted Brion was "cool on all fronts" about the proposed re-recording.

In late 2005 MTV News reported that Brion and Apple may collaborate again to complete the original recording sessions for Extraordinary Machine and release it officially in the near future.

[43] During mid-August 2005 and ahead of the album's release in October, both "O' Sailor" and "Parting Gift" were made available as a bundle download at the online iTunes Music Store.

While "O' Sailor" was released separately at other digital music stores, video promotion for "Parting Gift" began later that month.

[49] Apple also appeared on her own headlining summer tour from April 10, 2006 to October 29, 2006, with Damien Rice and Davíd Garza as her supporting acts for the 35 shows.